Yarn conditioning process



Patented Feb. .25, 1941- YARN CONDITIONING PROCESS Joseph B. Dickey, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y.,- a

corporation of New Jersey N 0, Drawing.

Application December 21, 1938, Serial No. 247,096

7 Claims. (Cl. 28-1) This invention relatesto the conditioning of textileyarns and more particularly to the conditioning of filaments and yarns composed of oranic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reducethe tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is' also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as stitch distortion," pin holes, laddering, and the like.

Heretofore it' has been proposed to employ softening agents such as polyhydricalcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal, or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which i high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufficlent solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying'agents in order to obtain operable yarn treating formulas. In addition, many of the known softening and lubricating agents are insufficiently soluble in water to permit satisfaca tory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn condition- 1 ing agents which are particularly adapted for the treatment of yarnscomposed of or containing 0 organic derivatives of cellulose and capable of which can be readily removed from the yarns by the usual scour baths. A still further object is action thereon.

to provide an improved method for the conditioning ofyarns, particularly those composed of or containing organic derivatives of cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including and particularly as softening agents, with or without the addition of animal, mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose. I have found that these compounds when employed as described in the detailed examples set forth below have a slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same time having too drastic an group with suitable phosphating agent such as phopshoric acid, phosphorus pentaoxide and sulfide, phosphorus oxychloride or derivatives, phosphorus thiochioride and derivatives, etc.

In addition to their use as yarn lubricants, I

have discovered that these compounds may also be employed as wetting-out, dispersing I and eulsifying agents, dye assistants, and as antistatic agents when applied to yarns particularly those composed of or containing organic derivatives of cellulose. Compounds of this type may be used in conjunction with older known textile lubricants such as blown and unblown teaseed, olive, sperm, neats-foot, peanut, soya bean and mineral oils.

Examples of the preparation of typical compounds ofthis type-are as follows:

Example 1 One mole of the dipalmityl ester of triethanolamine is dissolved in dioxane and six moles of pyridine are added. This solution is'added dropwise to a solution of one mole of phosphorus oxychloride in dioxane. The reaction is completed by warming and most of the dioxane and pyridine is removed under reduced pressure. Then a cold solution of sodium carbonate is added. The reaction product is triethanolamine dipalmitate phosphoric acid ester disodium salt and has the formula:

0 (CgHa-O--CuHu):

One mole of triethanolamine monocetyl sulionic acid ester having the formula:

N-CgHr-OH CaHaOH is reacted as described above with two moles of phosphorus thiochloride and the potassium salt prepared. The reaction product is trienthanolamine-bis-dipotassium thio-phosphate cetyl sulfonate ester and has the formula:

Cam-98:01.11 0 o Example 3 One mole of di-gamma-hydroxy propylaniline octadecyl sulfonate (prepared by treating digamma-hydroxypropylaniline with octadecanesulfonylchloride in. pyridine) and having the general formula:

is reacted as described in Example 1 with one mole methoxy phosphonyl dichloride and the ammonium salt, di-gamma-hy'droxy propylaniline-octodecylsulfonate a m m o n i u m phosphoric acid ester (monomethyi), prepared which has the formula c.mo-P ocm The phenyl group may contain a substituent such as COOH, -SO:H, C 1oHaa, -OC'1aHs7.-

etc.

Example 4 One mole of N-cyclohexyl-N-hydroxybutyl-N- hydroxy ethyl (B-a-naphthyl-keto propionate) having the formula is reacted with one mole of cetoxy chloride having the formula:

thiophosphory Example 3 C H10 H1 031140 E E H-C HEN-CaIId-O CaH n H One mole of the above compound, which is p-hydroxy ethyl p hydroxy-ethyl-fl-ethoxy ethyl tetrahydrofurfurylamine is reacted as in Example 1 with one mole of diamyl pho'sphamidyl dichloride having the formula and the tetrahydrofurfurylamine salt prepared. The reaction product is p-hydroxyethyl-p-hydroxyethyl p ethyl ethyl tetrahydrofurfurylaminediamyl phosphamate ester tetrahydrofurfurylamine salt. and has the formula:

Car-OH I CHr-CH| OH-NHa-CHr-CH CH:

Example 6 One mole of triethanolamine-octadecyl sulfonate-tetrahydrofuroate having the formula is reacted as in Example 1 with one mole of Mediethyl thlophosphamide" monochloride having the formula The reaction product is triethanolamine octadecyl sulionate-tetraehydrofuroate bisdiethyi thiophosphamate and has the formula: l.

/CIH|O-S-C1IHI1 N 0 CH:CB

One mole of triethanolamine-p-nitrophenoxy ether-oleyl ester having the formula:

CiHeOH is reacted as in Example 1 with one mole of cetyl phosphamyl dichloride having the formula:

and the morpholine, pyridine. piperidine, etc.

saltprepared. The reaction product is tripropanol-amine-p-nitro phenoxy-ether-oleyl ester cetyl phosphamyl ester morpholine saltand has the formula:

ake-Que,

oim-o-ccflml lm-o-r-n-onna olimorpholinc 'aasaoor The nitro group may be reduced, diarotired and copied to give oil-soluble dyes which are water so uble.

Example 9 One mole of p-nitrodi-p-hydroxy ethylaniline oleate having the formula:

is reacted as in Example 1 with one mole of dicetoxy phosphoryl chloride having the formula:

01 P-0 CuHa CnHn CIHIOH The reaction product is p-nitrodi-p-hydroxy ethyl aniline-oleate phosphate dicetyl ester and has the formula:

a lmf= o 16 M):

I The nitro group may be reduced, diazotized and coupled to give oil soluble dyes.

In accordance with the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. I have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably'are, employedas ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as lubricants.

m the following examples and description, I

have set forth several of the preferred embodiments of my invention, but they are included merely for purposes of illustration and not as a limitation thereof. I v

My invention will be more readily understood ,by reference to the following examples in which typical applications of the invention are set forth.

Eatample 10 Triethanolamine dioleate phosphate-dimethylcyclohexyl-amine salt having the formula:

is applied to textile material's (silk, wool, cotton,

viscose, cellulose acetate) by means of a bath,

wick. roller, spray, etc. to facilitate theirknitting, weaving, spinning and the like. Yarns lubricated with the above type of lubricant are of I special value in the preparation of cut staple fibers. These fibers may be oiled before or after cutting. a

Example 11 Example 14 Tri u dro th th 1 in t t i thi f but yl ii- 1.13m yam e m a e] Mum A conditioning liquid is made up as follows: cm-o-cusn-on Tetrahydrolurturyltetrahydrofuroate C,H O C,H O C CH' OKs-CH: om-om Pm ifffi on, $11-cm-o-0-(EK m so l o i o un-o-onn-o-r- 10 Wat v 10 s can Tgpmpanolamino oloate carats-phosphate dibutylamine t Noat's-ioot oil 97-88 0 HP 0 C .C "Ha Sodium sulfa 2 15 Example 15 15 Ethlhdr thl Hill 11 ht 1 CiH4 CCi1H i| te 'afiezhfifnm on im $3 053; 221 6 p 03p a e (b s CsH P B 20 QH|OP=(OH)I-IHN(CIHI)I]! w (c.HN-c,m-0P=[0H.N(-CHmOHh). fio 2o Blown neat's-ioot oil....; 89-65 Oleic acid 10-25 and applied to textile materials such assilk, wool,- Example 16 cotton, viscose. cellulose acetate, etc., as in Exspam on 49.20 25 ample 1. It the yarn is intended primarily for gg mggh xyethyisuocinate so knitting the amount of conditioning liquid Triethano laniine diaeetate phosphate potassium salt plied may vary from 445% by weight 01 the H yarn, and it for weaving between 1-5% by weight. 5 3 1 so Cellulose acetate filaments treated as described L 1-10 above are quite soft and pliable and give im- ,H| P Q K proved results in various textile operations such on as weaving, knitting, spinning, etc., and especially in the preparation 01 out staple fibers. Example 17 v Blown sperm oil.-. 86-73 Sulionatedcastor il 10 35 Cetyl sulfa l-5 E l 12 Triethanolamine dilaurate thiophosphate ammonium salt (C|H4-OCC|1H::): A conditioning liquid particularly useful in N 1-10 the preparation of out staple fibers made of Caro-P4! o cellulose acetate and which may be used for ONE. other textile operations is made up as follows: methylm 81ml sodium-mum 2 a Example 18 Pam Qtl-h :l% ethl diua hthe lamina h ht di ml 11 05 01M amusements, Y P P H a Y Di-B-hydroxyethyl cetyl amine monothio'phosphate Naphtmyl 7 /0H l- N/Ca'Hc-OH c,Hro P\ )u-u 1-10- Ho Naphthenyl A on. N- mmromu 50 L -E ZJ I Mineral oil 10 0 Example 19 s re at:

ll ['0 Other examples of yarn conditioning composi- Triethanolaminc dinnphtheuate phosphate sodium m: 55

tions which may be applied to various types of 0H yarns, particularly those composed 01' or con- 1, taining cellulose acetate. cellulose acetate propionate, celluloseacetate butyrate and similar N: 0-Na 1-10 cellulose organic acid esters in accordance with my invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, and 7 2 18 2 the manufacture of cut staple fibers, are as fol- Triethanolamine naphthcnate pyrophosphate sodium salt 65 ows:

Example 13 on-om c,11n-oi -o--P=o Pm. N-N-d ibutylpropanolamine-disodium phosphate H OH 140 -CrHr-O'C-naphthenyl /N'c1Hl ol PM CIHIOH CiHc 'ONa 1-10 1 u a Blown olive il 79-60 fififi fimm f3 Ethanolamine propionate butyrate....' 20-30 Blown sperm oil. 59-40 1 Example 21 I Parts Li ht mineral no I oo Tr ethsnolamine naphthenate oleate phosphate diethylcyclo hexylamine salt olnigo-b-m mhon i Water I I I Water soluble cellulose ester I suifonated castor oil Bets-hydroxy ethyl dilietrahydromriurylamino thio phosphatedipotassiums sin-Pain CH:CH

n, tn-,cni-N o11r-tH tn, elm-or o v Any'of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath; wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 23-25% by weight of the yarn. Usually, however, the amountjof conditioning liquid'applied is about 10-15% by weight of theyarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when'used in the circular knitting process, 7

As will be apparent from the above examplesand description the conditioning agents of my bringing the yarn in contact with a wick, roll,

or felt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the' godet orother roll or guide-and the point of winding and/or twisting. In some cases, the

liquid may even be applied to the yarn after winding onto cones; spools, bobbins, or the like or by the so-called ."bobbin .to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon the result desired, the

specific nature of t the material to which the yarn is intended for weaving, the amount may I vary between about 1 and 5%.

Although in the'above examples I. have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, nonsolvents, emulsifying agents, blending; agents and the like, m y be added within the scope of my invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although I have found it convenient to illus-. trate my invention by reference to compositions containing specific percentages of the various in gredients,these percentages may vary widely depending .upon the particular purpose for which the composition is-intended. For example, if it is desired to cont ol the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by

reducing the amount of the agent and'corre- 5 spondingly increasing the amount of oil or other ingredient.

While I have described my invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivative. yamssuch as those composed of or containing cellulose propionate, cellulose butyr-' ate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of'a thread,,either of high or low twist,

single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials,

as well as out staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above, the yarn conditioning agentsof my invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such'as cottonseed, olive, castor, neat'sfoot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition.

The yarn conditioning method and composi tions of my invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordas cellulose acetate and render'them amenable to various textile operations, especially operations such as those involved in the manufactureof cut staple fibersand in weaving and knitting. Another outstanding characteristic of these comwide variety of mineral, animal, and vegetable pounds is their exceptional solvent power for a oils and their ability to act as lubricating assist- I ants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of myinvention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from de fects such as pin holes,v stitch distortion, laddering and the like.

What I claim is: y

l. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning, themanufacture of staple fibers, and the like, which comprises applying a lubricating and anti-static composition containing as its essential lubricating and antistatic component an ester selected from the group consisting of phosphate and thiophosphate esters of partially esterified hydroxy tertiary alkanol amines.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like which comprises applying a lubricating and anti-static composition containing as its essential lubricating and anti-static component an ester selected from the group consisting of the phosphate and thicphosphate esters of partially esterifled hydroxy tertiary alkanol amines.

3. The process of conditioning yarn composed of or containing cellulose acetateto render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying a lubricating and anti-static composition containing as its essential lubricating and antistatic component an ester selected from the group consisting of phosphate and thiophosphate esters' of partially esterifled hydroxy tertiary alkanol amines.

4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like which comprises applying a lubricating and anti-static-composition containing as its essential lubricating and antistatic component an ester selected from the group of phosphate and thiophosphate esters oi partially esterified hydroxy tertiary alkanol amines and a textile lubricant.

5. Textile yarns amenable to textile operations including knitting, weaving, spinning, the manufacture oi. staple fibers, and the like impregnated with a lubricant and anti-static composition containing as its essential lubricating and anti-static component an ester selected from the group consisting of the phosphate and thiophosphate esters of partially esterified hydroxy tertiary alkanol amines.

6. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like impregnated with a conditioning agent comprising an ester of phosphate and thiophosphate JOSEPH B. DICKEY. 

